Methanol → HCID 9834518, compound

HRID 1582443Notes

Reaction equation

HRID 1582443 reaction equation
FC(F)(F)C([N:5]1[CH2:18][CH2:17][C:9]2=[CH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1)=O.ClS([N:25]=[C:26]=[O:27])(=O)=O.CO.C[O-].[Na+]>ClCCl>[CH2:17]1[C:9]2=[C:10]([C:26]([NH2:25])=[O:27])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6][NH:5][CH2:18]1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 70918Chlorosulfonyl isocyanateHCID 9921822HCID 9921822, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 9834518HCID 9834518, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,2,2-trifluoro-1-(1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol-3-yl)-1-ethanone (448 mg, 1.6 mmol) in dichloromethane (20 mL) is treated with chlorosulfonyl isocyanate (0.19 mL, 2.1 mmol). The resulting golden homogenous solution is stirred for 1 hour and treated with methanol (10 mL) and a solution of 25% sodium methoxide in methanol (2 mL, 8.8 mmol). The reaction mixture quickly turns to a white suspension and after 30 min is filtered to give a crude white solid. This material is triturated with hot methanol, filtered through a pad of celite, and concentrated to 184 mg of a white solid that is further purified by LC (230-400 silica gel) eluting with 9:1:89 methanol/NH4OH/dichloromethane to afford 137 mg of 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carboxamide as a white solid. IR (drift) 3353, 3341, 3173, 1641, 1602, 1549, 1463, 1432, 1418, 1322, 1314, 778, 740, 729, 654 cm−1.

Workup

  1. waitThe reaction mixture quickly turns to a white suspension and after 30 min
  2. filtrationis filtered
  3. customto give a crude white solid
  4. customThis material is triturated with hot methanol
  5. filtrationfiltered through a pad of celite
  6. concentrationconcentrated to 184 mg of a white solid
  7. customthat is further purified by LC (230-400 silica gel)
  8. washeluting with 9:1:89 methanol/NH4OH/dichloromethane

Sources & evidence

ORD record
ord-b4aab87281494ab6923cae0d0047cc3d
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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